136013-95-1Relevant articles and documents
Isomerization of all-(E)-retinoic acid mediated by carbodiimide activation synthesis of ATRA ether lipid conjugates
Christensen, Mikkel S.,Pedersen, Palle J.,Andresen, Thomas L.,Madsen, Robert,Clausen, Mads H.
scheme or table, p. 719 - 724 (2010/03/24)
Treatment of the lysolipid 1-O-hexadecyl-sn-phosphatidylcholine with all-(E)-retinoic acid, DCC and DMAP resulted in poor acylation and caused (Z)Z(E) isomerization of the α-β double bond. In the presence of a proton, source, the carbodiimide-activated all-(E)-retinoic acid undergoes fast isomerization to give a final mixture of (13E)/(13Z) isomers in a 3:1 ratio. Similar treatment of (13Z)-retinoic acid leads to the same isomer ratio. The isomerization was circumvented successfully by using a Mitsunobu reaction, which provided an efficient synthesis of all-(.E)-retinoic acid sn-2-conjugated to phosphatidylcholine and phosphatidylglycerol etherlipids.